Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
- Date Wed 16th September 2026 - Sat 24th October 2026
- Time 5:30PM EDT
- Location Cheshire, Connecticut
- Price Free - $41.28
- Races 5 races
- Distances 5km
Event summary
Join us for the vibrant Cheshire Community YMCA Harvest Trail Race and Y Cup Relay, taking place from September 16 to October 24, 2026, in the picturesque Naugatuck Valley at historic Ives Farm. This exciting event is perfect for all ages, featuring a scenic 5K run and a fun-filled Fit N Fun Adaptive 1.5K, ensuring everyone can participate and enjoy the festivities. The race kicks off with a FREE Pumpkin Dash for kids aged 6 and under at 9:45 AM, followed by the 5K at 10:00 AM and the Y Cup Relay at 10:05 AM.
Get ready for a day packed with family-friendly activities, including pumpkin decorating, face painting, Halloween mask making, games, live music, and a delightful fall-themed photo booth. All proceeds from the event will support the vital work of the YMCA in the Cheshire community and contribute to the revitalization efforts of the Ives Farm property by the Cheshire Land Trust. Don't miss this opportunity to celebrate community spirit, health, and the beautiful fall season!
Get ready for a day packed with family-friendly activities, including pumpkin decorating, face painting, Halloween mask making, games, live music, and a delightful fall-themed photo booth. All proceeds from the event will support the vital work of the YMCA in the Cheshire community and contribute to the revitalization efforts of the Ives Farm property by the Cheshire Land Trust. Don't miss this opportunity to celebrate community spirit, health, and the beautiful fall season!
Organiser's Description
The Cheshire Community YMCA and Cheshire Land Trust are partnering on a race around historic Ives Farm. This all-ages run will wind through the fields and trails on the property, with the start and finish line located at the beautifully restored barn. Proceeds from this event will support the work that the YMCA does in the Cheshire community as well as the revitalization plans that the Cheshire Land Trust has for the Ives Farm property.
* Prior to the race there will be a FREE Pumpkin Dash for kids 6 years old and younger.
* Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth
Pumpkin Dash Start: 9:45AM
5K Start: 10:00AM
Y Cup Relay Start: 10:05AM (All Y-Cup Runners must arrive by 8:45AM at the latest. Participants leave for their relay position by 9:15AM)
Fit N Fun Adaptive 1.5K 10:10AM
* Prior to the race there will be a FREE Pumpkin Dash for kids 6 years old and younger.
* Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth
Pumpkin Dash Start: 9:45AM
5K Start: 10:00AM
Y Cup Relay Start: 10:05AM (All Y-Cup Runners must arrive by 8:45AM at the latest. Participants leave for their relay position by 9:15AM)
Fit N Fun Adaptive 1.5K 10:10AM
Races
-
5K Trail Race
Incl. $3.28 Fee & Custom Harvest Trail Race Hat
Sat 24th October 2026 (10:00AM EDT)
$41.28
CLOSEDThis is a 5k trail race with varied terrain and slight elevation which winds through groomed wooded paths and open fields - perfect for the road runner wanting to try a trail run. It's also a good opportunity for an experienced trail runner to do some speed work. -
Y Cup Relay
Incl. $2.02 Fee & Custom Harvest Trail Race Hat
Sat 24th October 2026 (10:05AM EDT)
$19.02
CLOSEDTeams of 3 elementary school students will each run one mile of the 5K course. Teams from all grades will compete for their team to determine which school wins the prestigious Y Cup for the 26-27 school year. (All Y-Cup Runners must arrive by 8:45AM the latest. Participants leave for their relay position by 9:15AM) -
Pumpkin Dash
Incl. Finisher Medal
Sat 24th October 2026 (9:45AM EDT)
Free
CLOSEDA free race for children 6yr and younger on the dirt path around the historic Ives Farm barn. Young runners will end the dash by running through the same race finish line as all other racers! -
Fit N Fun Adaptive 1.5K Run
Incl. $2.02 Fee & Custom Harvest Trail Race Hat
Sat 24th October 2026 (9:55AM EDT)
$19.02
CLOSEDGet ready for a fun fall adventure! An extension of our Fit & Fun program, this adaptive 1.5K takes participants off road through open fields and groomed wooded paths, with grass and uneven ground along the way. Each participant will have a dedicated volunteer buddy by their side to cheer them on and help them reach the finish line. -
5K FREE - 6 Week Training Series Dates 9/16, 9/23, 9/30, 10/7, 10/14, 10/21
Wed 16th September 2026 (5:30PM EDT)
Free
CLOSEDThis is a FREE 6-week training series for runners looking to prepare for the 5K Harvest Trail Race, improve their fitness, and train alongside others in a supportive environment. All sessions will be conducted at: 435 North Brooksvale Rd. Cheshire, CT 06410
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1585 Cheshire St., Cheshire, 06410, CT, United States
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Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
